Determination of the absolute configuration of primary amines in polar NMR solvents

Hee Choon Ahn, Kihang Choi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

N-(2-Nitrophenyl)proline (2-NPP) can be used in a wide range of solvents as an effective chiral auxiliary for the absolute configuration assignment of a-chiral primary amines. Even in competitive hydrogen-bonding solvents, 2-NPP amides of primary amines retain the conformation preference for intramolecular hydrogen bonding and produce significant anisotropic effects on the amine substituents. As a result, the absolute configuration can be assigned by comparing the ' H NMR spectra of diastereomeric 2-NPP amides recorded in polar NMR solvents.

Original languageEnglish
Pages (from-to)1330-1331
Number of pages2
JournalChemistry Letters
Volume36
Issue number11
DOIs
Publication statusPublished - 2007 Nov 5

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Amines
Nuclear magnetic resonance
Amides
Hydrogen bonds
Conformations
N-(2-Nitrophenyl)proline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Determination of the absolute configuration of primary amines in polar NMR solvents. / Ahn, Hee Choon; Choi, Kihang.

In: Chemistry Letters, Vol. 36, No. 11, 05.11.2007, p. 1330-1331.

Research output: Contribution to journalArticle

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